New Chicago Holidays

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    Better together

    Save up to €185 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in New Chicago

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
18 Sept - 22 Sept
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Doorman was delightful! King room was spacious. Toilet flush was problematic. The pool was not open despite the advertisement on the Expedia websit. Lots of additional, non-negotiable charges once you get there.

Reviewed on 11 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
18 Sept - 22 Sept
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Amazing property well worth the money

Reviewed on 11 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
18 Sept - 22 Sept
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
18 Sept - 22 Sept
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
We enjoyed the rooftop dining--the view is terrific, especially after dark. Excellent location on Michigan Ave near restaurants, shopping and museums. Did the valet parking and it worked well for us. The service was all around excellent including checkin/checkout, in room dining service (we did breakfast), concierge, baggage help and valet . They were able to give us a late check out so we could fit in an architectural boat tour and then kept our luggage all day until evening so we could squeeze more out of this long weekend trip to the Windy City. The hotel is clean, stylish and service is top rate. I would highly recommend this hotel.

Reviewed on 11 Aug 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
18 Sept - 22 Sept
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
Beautiful hotel in great location. The food option at hotel are great with good food. It is walkable to surrounding attractions.

Reviewed on 10 Aug 2025

Top hotels in New Chicago

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd., East Chicago, IN
Fully refundableReserve now, pay when you stay
The price is €124 per night from 1 Sept to 2 Sept
€124
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"It was very nice , smaller casino great service at the bar !! Very friendly people"

Reviewed on 7 Aug 2025

Ameristar Casino Hotel East Chicago
Super 8 by Wyndham South Holland

Super 8 by Wyndham South Holland

2 out of 5
17225 Halsted St, South Holland, IL
Fully refundableReserve now, pay when you stay
The price is €74 per night from 20 Aug to 21 Aug
€74
20 Aug - 21 Aug
includes taxes & fees
7.2/10 Good! (1,000 reviews)
"This was a little bit of hair in the tub but over all it was a very nice room! Nice area as well!"

Reviewed on 4 Aug 2025

Super 8 by Wyndham South Holland
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is €109 per night from 2 Sept to 3 Sept
€109
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"I feel better breakfast options but everything else was perfect"

Reviewed on 10 Aug 2025

Spring House Inn
See all 473 properties in New Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a New Chicago holiday package cost?
You can snap up a holiday package to this destination from €727 on Expedia. But how much your holiday to New Chicago costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to New Chicago?
January, February and September are great times to look for cheap New Chicago holiday packages. Travelling in quieter months means you can usually find lower prices on flights and hotels.
How many days is enough for New Chicago?
With a well-organised schedule, you can easily visit the top New Chicago sights in a handful of days. But if you prefer to discover hidden spots or go on day tours, consider booking your New Chicago holiday for longer.
How to find the best New Chicago package deals?
Begin your search for a New Chicago package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect New Chicago package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your New Chicago adventure off to a flying start.
Is it cheaper to book a New Chicago holiday as a package?
You can enjoy significant savings on your New Chicago escape by booking a personalised holiday package. Check the "Package" heading, then enter your travel dates and destination to view some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to New Chicago?
If you're considering an impromptu New Chicago holiday, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to New Chicago?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to New Chicago.
  2. Work out your budget: Make sure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your hotel will likely be the biggest expense during your trip to New Chicago.
  3. Determine how many days away: Start by compiling a list of the attractions you'd like to get to in New Chicago. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalised New Chicago holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.